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Triethylamine → tert-butyl (3R)-3-[[(1S)-1-(4-methoxycarbonylphenyl)ethyl]carbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate

HRID 2205303
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HRID 2205303 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:17]([C:18](O)=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:36][C@H:37]([C:39]1[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][CH:40]=1)[CH3:38]>ClCCl>[CH3:46][O:45][C:43]([C:42]1[CH:47]=[CH:48][C:39]([C@@H:37]([NH:36][C:18]([C@H:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:19])[CH3:38])=[CH:40][CH:41]=1)=[O:44]
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HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 688607(3R)-2-[(tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 17751895Methyl 4-((1S)-1-aminoethyl)benzoate

생성물 1

HCID 131735812tert-butyl (3R)-3-[[(1S)-1-(4-methoxycarbonylphenyl)ethyl]carbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate수율 97%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a 0° C. mixture of (3R)-2-tert-butoxycarbonyl-3,4-dihydro-1H-isoquinoline-3-carboxylic acid (40.0 g, 141.4 mmol) and dichloromethane (784 mL), add triethylamine (21.7 mL, 155.5 mmol). Then add isobutyl chloroformate (20.3 mL, 155.5 mmol) in a dropwise fashion. After the end of the addition, stir the mixture at 0° C. for 20 minutes. Then, add methyl (S)-4-(1-aminoethyl)benzoate (27.9 g, 155.5 mmol), and stir the mixture at room temperature for 1 hour. Add water (400 mL), separate the layers, and wash the organic layer with 1 M aqueous KHSO4 (500 mL), followed by saturated aqueous NaHCO3 (500 mL). Dry the organic phase over MgSO4, filter to remove the solids, and concentrate the filtrate under reduced pressure to furnish the title compound as a white solid (60 g, 97% yield). Mass spectrum (m/z): 339 ([M+H−Boc]+), 383 ([M+H−t-Bu]+), 439 ([M+H]+).

후처리

  1. additionAfter the end of the addition
  2. stirringstir the mixture at room temperature for 1 hour
  3. customAdd water (400 mL), separate the layers
  4. washwash the organic layer with 1 M aqueous KHSO4 (500 mL)
  5. dry with materialDry the organic phase over MgSO4
  6. filtrationfilter
  7. customto remove the solids
  8. concentrationconcentrate the filtrate under reduced pressure

출처 및 근거

ORD 기록
ord-b6249fa7f1934afca45498f0dc0f3cce
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09371289B2

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